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J Org Chem. 2001 Nov 30;66(24):8094-100.

Controlling factors in the synthesis of cucurbituril and its homologues.

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School of Chemistry, University College, University of New South Wales, Australian Defence Force Academy, Canberra, ACT 2600, Australia.


The acid-catalyzed synthesis of cucurbit[n]urils from formaldehyde and glycoluril is poorly understood. In this paper, we examine a wide range of reaction conditions that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5-10. A mechanism for the formation of these cucurbit[n]urils is presented. Individual cucurbit[n]urils were unambiguously identified in reaction mixtures using ESMS and (13)C NMR.


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